Yes to the first question. Set up a Virtual Axis to execute your AXIS commands, then take that axis CurrentVelocity value and scale it to give you a value for your analog output. I have done this with a hydraulic system that is controlled by a proportional valve, with an encoder to close the loop, and it worked excellently.
To your second question, it is not possible to directly close the loop with an analog input, when using the high speed axis setup. I believe it should be possible to use an open loop axis configuration, and then add some math based on your analog position input, to trim the analog output to the VFD based on the analog position feedback. I've never done it though, and as mentioned it may be simpler to solve this application some way other than using AXIS commands.